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Cheap flights from South Africa to Chicago from R12 546

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from South Africa to Chicago departing on 9/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from South Africa to Chicago

Recent return flight deals from South Africa to Chicago

Enter your travel dates to find the best prices.
Delta Logo
20:05 - 21:09
CPT
-
MDW
32h 04m
1 stop
Delta Logo
10:55 - 17:50
MDW
-
CPT
23h 55m
1 stop
R16 645Delta
Sun, May 31 - Sat, Jun 13
Delta Logo
20:05 - 18:33
CPT
-
MDW
29h 28m
2 stops
Delta Logo
13:26 - 17:50
MDW
-
CPT
21h 24m
2 stops
R17 911Delta
Sun, May 31 - Sat, Jun 13
Delta Logo
20:25 - 18:18
JNB
-
MDW
28h 53m
2 stops
Delta Logo
18:55 - 10:25
MDW
-
JNB
32h 30m
2 stops
R19 927Delta
Sun, Jun 7 - Sat, Jun 20
Delta Logo
21:55 - 16:16
JNB
-
MDW
25h 21m
1 stop
Delta Logo
18:55 - 10:25
MDW
-
JNB
32h 30m
2 stops
R21 327Delta
Sun, Jun 7 - Sat, Jun 20
Virgin Atlantic Logo
20:05 - 22:17
CPT
-
MDW
33h 12m
1 stop
Virgin Atlantic Logo
16:25 - 17:50
MDW
-
CPT
18h 25m
1 stop
R22 426Virgin Atlantic
Sun, Jun 21 - Sat, Jul 4
Virgin Atlantic Logo
20:25 - 21:46
JNB
-
MDW
32h 21m
2 stops
Virgin Atlantic Logo
17:25 - 19:40
MDW
-
JNB
19h 15m
1 stop
R23 343Virgin Atlantic
Thu, Sep 3 - Sun, Sep 13
KLM Logo
23:15 - 18:18
CPT
-
MDW
26h 03m
2 stops
KLM Logo
12:50 - 21:25
MDW
-
CPT
25h 35m
2 stops
R24 792KLM
Wed, Jun 10 - Wed, Jun 17
KLM Logo
23:15 - 18:18
CPT
-
MDW
26h 03m
2 stops
KLM Logo
12:50 - 21:25
MDW
-
CPT
25h 35m
2 stops
R26 258KLM
Wed, Jun 10 - Wed, Jun 17
KLM Logo
23:15 - 18:18
CPT
-
MDW
26h 03m
2 stops
KLM Logo
12:46 - 21:25
MDW
-
CPT
25h 39m
2 stops
R26 658KLM
Mon, Jul 13 - Wed, Aug 12
Virgin Atlantic Logo
21:55 - 16:15
JNB
-
MDW
25h 20m
1 stop
Virgin Atlantic Logo
17:10 - 19:40
MDW
-
JNB
19h 30m
1 stop
R26 925Virgin Atlantic
Mon, Jul 6 - Tue, Jul 21

KLM flights from South Africa to Chicago Midway Airport

Our best KLM deals on South Africa to Chicago Midway Airport flight tickets
KLM
May 28
CPT23:15Cape Town Intl
25h 41m
2 stops
MDW17:56Chicago Midway
Jun 4
MDW13:22Chicago Midway
25h 03m
2 stops
CPT21:25Cape Town Intl
R21 327
KLM
May 28
CPT23:15Cape Town Intl
25h 41m
2 stops
MDW17:56Chicago Midway
Jun 4
MDW13:22Chicago Midway
25h 03m
2 stops
CPT21:25Cape Town Intl
R23 876
KLM
May 28
CPT23:15Cape Town Intl
25h 41m
2 stops
MDW17:56Chicago Midway
Jun 4
MDW13:22Chicago Midway
25h 03m
2 stops
CPT21:25Cape Town Intl
R24 992

Virgin Atlantic flights from South Africa to Chicago Midway Airport

Our best Virgin Atlantic deals on South Africa to Chicago Midway Airport flight tickets
Virgin Atlantic
Sept 3
JNB20:25Johannesburg OR Tambo
32h 21m
2 stops
MDW21:46Chicago Midway
Sept 13
MDW17:25Chicago Midway
19h 15m
1 stop
JNB19:40Johannesburg OR Tambo
R23 343
Virgin Atlantic
Jul 6
JNB21:55Johannesburg OR Tambo
25h 20m
1 stop
MDW16:15Chicago Midway
Jul 21
MDW17:10Chicago Midway
19h 30m
1 stop
JNB19:40Johannesburg OR Tambo
R26 925
Virgin Atlantic
Jul 22
JNB20:25Johannesburg OR Tambo
32h 50m
2 stops
MDW22:15Chicago Midway
Jul 28
MDW17:10Chicago Midway
19h 30m
1 stop
JNB19:40Johannesburg OR Tambo
R27 625

momondo Fare Finder

 
Customise your flight search to find flights from South Africa to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 13 550 searches. Data last updated 20 May 2026.
Use the filters below to find and compare flights from South Africa to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Sun 31/5

20:05-21:09

1 stop32h 04m

Chicago Midway

Sat 13/6

10:55-17:50

1 stop23h 55m

R16 645

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Sun 31/5

20:05-18:33

2 stops29h 28m

Chicago Midway

Sat 13/6

13:26-17:50

2 stops21h 24m

R17 911

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Sun 7/6

20:25-18:18

2 stops28h 53m

Chicago Midway

Sat 20/6

18:55-10:25

2 stops32h 30m

R19 927

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Sun 7/6

21:55-16:16

1 stop25h 21m

Chicago Midway

Sat 20/6

18:55-10:25

2 stops32h 30m

R21 327

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Sun 21/6

20:05-22:17

1 stop33h 12m

Chicago Midway

Sat 4/7

16:25-17:50

1 stop18h 25m

R22 426

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Thu 3/9

20:25-21:46

2 stops32h 21m

Chicago Midway

Sun 13/9

17:25-19:40

1 stop19h 15m

R23 343

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Wed 10/6

23:15-18:18

2 stops26h 03m

Chicago Midway

Wed 17/6

12:50-21:25

2 stops25h 35m

R24 792

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Wed 10/6

23:15-18:18

2 stops26h 03m

Chicago Midway

Wed 17/6

12:50-21:25

2 stops25h 35m

R26 258

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Mon 13/7

23:15-18:18

2 stops26h 03m

Chicago Midway

Wed 12/8

12:46-21:25

2 stops25h 39m

R26 658
Fastest return journey

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Mon 6/7

21:55-16:15

1 stop25h 20m

Chicago Midway

Tue 21/7

17:10-19:40

1 stop19h 30m

R26 925

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from South Africa to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from South Africa to Chicago Midway?

Virgin Atlantic, KLM, and Delta are the most popular carriers operating from South Africa to Chicago Midway

Cheap South Africa to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from South Africa to Chicago Midway Airport

Fastest flight time

21h 02m

Direct flights

None
The fastest flight from South Africa to Chicago Midway Airport takes 21h 02m
There are no direct flights from South Africa to Chicago Midway Airport. There are no popular flight routes from South Africa to Chicago Midway Airport.
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Frequently asked questions about flying from South Africa to Chicago Midway Airport

  • When did momondo last update prices for flights from South Africa to Chicago Midway Airport?

    Prices for flights from South Africa to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from South Africa to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and stopovers. It is recommended that you verify with the airline you are booking with for travel from South Africa to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's licence and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond

Why use momondo?

Why should I use momondo to find a flight deal from South Africa to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from South Africa to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from South Africa to Chicago with flexible booking policies on momondo?

Flights from South Africa to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from South Africa to Chicago?

momondo helps you find the best flight between South Africa and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from South Africa to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from South Africa. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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